Clean Yourself

This is not technically wardrobe advice, but must be stated nonetheless. It does not matter how good your fit is–if you smell bad, the point is moot. Simple things—doing your hair, cleaning yourself properly, making sure your clothes are wrinkle free—go a long way. If your favorite tee, shirt or pants are dirty, even if they perfectly compliment your footwear, either wash them or leave them at home. While hygiene is usually out of our purview, a few simple tips go a long way. Wash your face, throw on a facemask, deep condition your hair if you have to. Anything that will help make your sparkle. It makes a difference.

Groom Yourself

This falls along the same lines as what was previously mentioned, but whether it means getting a haircut, trimming your beard or shaving your legs—we don’t judge—make sure you’re as well-cut as humanly possible. It’s the small details that set you apart, and the “rough around the edges" look might work for, say, Chris Hemsworth as Thor, but it will most certainly not work for the rest of us. Plus, a fresh haircut always makes you more confident which can never hurt, especially on a first date.

Be Yourself

It’s easy to immediately go for the “nicest” outfit in your wardrobe. Avoid the temptation. While in theory your best suit may very well work, if it’s not something you wear regularly, you may look uncomfortable—or worse, awkward—which is the worst possible scenario. Think of the nicest possible version of what you wear on a daily basis, and that should be exactly what you wear. The best way to be yourself is to be comfortable. A luxe version of your daily attire will not only do just that, but act as a physical expression of your personality, a poster board for your authentic self. Your date will appreciate it.

Where you choose to meet is simultaneously the most and least important part of any date. A bad decision—say, taking someone who hates sports to a college bar during the playoffs or a vegan to a steakhouse—can be disastrous, while a good one can salvage a lack of chemistry. That said, if you truly get along, it doesn’t matter where you go. Our advice? Keep it simple, and head somewhere full-proof. An ice cream parlor, coffee shop or no-fuss but delicious casual restaurant. Each is low stress, non-threatening and sets exactly the tone you’re looking for. If you ignore all of our advice and already have a place in mind, just make sure your wardrobe is suited for the occasion. If you are going ice-skating (cliche, but sure), don’t wear shorts. If you’re headed to the movies, bring a sweater. If you’re going out to a formal dinner, consider wearing a blazer. Little details ensure that you don’t look wildly out of place.

Casual

Like we mentioned, venue dictates the wardrobe. If you were smart enough to follow our advice and go somewhere with low stakes, than a casual outfit will perfectly compliment the convivial nature of the date. If you have a style preference, stick to it—again, be yourself–but try to hone in and elevate your everyday wardrobe. If your day-in day-out look is trousers and sneakers, consider wearing a brand new pair of sneakers (or relatively new to avoid awkward "did you just buy those" questions). If you tend to skew towards avant-garde fashion or techwear, try and go as subtle as possible. If you wear Americana, some great denim, a trucker and your favorite boots is perfect. For those who need some help, we recommend an outfit that highlights you, rather than the clothes themselves. Consider some Margiela GAT Replica sneakers, black trousers and fitted blank T-shirt. If it's cold, a trucker jacket—either a vintage one from Levi's or a perfectly faded Visvim number—looks good on literally everyone. Remember, this person is here to spend time with you, not your outfit, so try to not overthink it. You'll be just fine.

“Date Night”

A dated trope, but the "date night" expression exists for a reason. Depending on who you ask out (or where you end up meeting), your date may immediately think that your outing necessitates getting "dressed up." While we don't necessarily agree with the concept—or even the idea of clothes for "special occasions" for that matter–we don't make the rules, and nothing is worse than being underdressed. If you're meeting someone for a drink or simply feel the date requires a bit of sprucing up, an unstructured blazer elevates an outfit without screaming formal. While the suit and T-shirt concept is overplayed, it still works, so if you happen to own a slim suit by say, Dries Van Noten, Dior or Saint Laurent, pair it with your best black T-shirt and penny loafers and you're good to go.

Formal Dinner

If for some odd reason you chose to go to a formal sit-down restaurant on a first date, it's okay—we all make mistakes. That said, you're still going to need something to wear. While the aforementioned T-shirt and suit combo probably feels a bit too laid back, a full on suit-and-tie can feel way too stiff (unless that's your entire aesthetic, then by all means go for it). Our recommendation, consider alternative suiting options. Brands like Camoshita and Eidos make suits with considerably more character than many sartorial counterparts. Rather than a standard button up shirt, consider a knit polo or thin sweater—both equally as elegant yet not quite as staid. As this is a formal restaurant or event, stick to darker hues but avoid black if you can, it may feel a tad too nuptial.